When a “Good Enough” Prompt Is Not Enough: Why I Built Photo Whisperer as a Custom GPT
After months of decoding court records and hundreds of newspaper clippings for my book The Solomon Gang: Outlaws by Any Name, I turned my attention to the historical family photos that appear throughout the manuscript. These old images had always fascinated me, but many lacked dates, captions, or context.
Out of curiosity, I tried using AI to analyze one of them — and the results were far better than I expected. That experience showed me the power of AI for historical photo analysis. It also showed me that most people would never think to write the long, expert-level prompts needed to get consistent, accurate results.
So I built Photo Whisperer, a custom GPT designed specifically for dating and placing old family photos. It’s essentially a prompt on steroids: all the expertise, structure, and careful instructions are baked in, so you can simply upload a photo and get a full, reasoned analysis without knowing anything about prompt engineering.
Using Photo Whisperer on the “Staged Mugging” Photo
For this post, I ran one of my favorite images through Photo Whisperer — the playful “staged mugging” portrait of two young men in a studio, one pointing a pistol at the other. Based on family knowledge, I believe the men are my great grandfather (born 1875) and his brother (born 1878), photographed during their early outlaw years. They were only together, and not incarcerated, prior to 1904, which already helps narrow the timeframe.
The date of this photo is especially important to me, because establishing when it was taken helps clarify the timeline of the brothers’ movements in the brief period before their eventual incarceration.
Here’s what Photo Whisperer came back with.
Date Estimate: Circa 1898–1908, with the strongest likelihood 1900–1905.
Probable Origin: A professional American studio offering novelty or comedic portraits. Staged “hold-up” scenes were especially popular in small-town and Western U.S. studios around the turn of the century.
That was remarkably accurate. The style of clothing, the hats, the studio backdrop, and the novelty pose all match what we know of the brothers — and the era they were active together. Photo Whisperer also returned extensive detail about their clothing, their posture and actions, the likely type of photograph, and the probable date range. And in the end, the final analysis was strikingly accurate.
Asking Photo Whisperer to Re-Date the Photo Using Age Information
Next, I provided the model with the birth years:
Left man: born 1875
Right man: born 1878
Then I asked it to estimate their ages in the photo, and to re-evaluate the likely date based on that clue.
Here is what it produced:
Age Analysis
Photo Whisperer estimated both men were in their early to mid-20s, and gave the following timeframe based on their ages:
If the photo shows:
Left man (b. 1875): age 22–27 → years 1897–1902
Right man (b. 1878): age 19–24 → years 1897–1902
The ranges overlap perfectly.
The model also noted that this updated date range is fully consistent with:
Jacket and collar styles
Haircuts and mustaches
Studio lighting and painted backdrop
The popularity of novelty “buddy” portraits during this era
Final Assessment (Updated With Age Data)
Taking into account:
Their known birth years (1875 and 1878)
Their apparent youthful ages
Clothing and hairstyle clues
Studio setting and photographic format
Photo Whisperer concluded:
The photo was almost certainly taken between 1897 and 1902. Most likely: circa 1900.
This lines up beautifully with everything we know about the brothers’ movements during that window — including the fact that they were together, not yet in prison, and very much in their mischievous prime.
In future posts, I’ll share more Photo Whisperer analyses from my family collection. Old photos carry clues most of us overlook, and AI is proving to be an incredibly helpful junior researcher when those clues start coming together.
